1-(Isocyanatomethyl)-3-methoxybenzene → 3-(3-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098288노트

반응식

HRID 2098288 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]=[C:8]=[O:9].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]1[C:8](=[O:9])[N:19]2[CH:18]=[N:17][C:16]([C:20]([NH2:22])=[O:21])=[C:15]2[N:13]=[N:14]1

참가 물질

4

반응물 2

HCID 36446341-(Isocyanatomethyl)-3-methoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

생성물 1

HCID 441283783-(3-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Meta-methoxybenzyl isocyanate (Sigma Aldrich) (0.390 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product (off-white) removed by filtration, washed with water and ethyl acetate, and recrystallised from chloroform. Yield: 0.335 g, 56%. IR vmax/cm−1 3092, 1730, 1678, 1601. 1H NMR δH (DMSO-d6) 3.76 (3H, s, Me), 5.49 (2H, s, CH2Ar), 6.89-6.92 (1H, m, ArH), 7.00-7.02 (1H, m, ArH), 7.28-7.32 (1H, s, ArH), 7.70 (1H, br s, NH), 7.82 (1H, br s, NH), 8.84 (1H, s, 6-H). δC (DMSO-d6) 52.2, 55.6, 113.7, 114.0, 120.4, 129.5, 130.1, 131.4, 134.9, 137.6, 139.7, 159.9, 162.0. Found 301.1091. Calc for (M+H): 301.1049. Found C, 51.3; H 3.9; N 27.8. Calc. for C13H12N6O3C, 52.0; H, 4.0; N, 28.0%.

후처리

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product (off-white) removed by filtration
  3. washwashed with water and ethyl acetate
  4. customrecrystallised from chloroform

출처 및 근거

ORD 기록
ord-cdd16747ee244d7eaed8ddc9b311da1c
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450479B2

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